Summerland Key Squirrel Key Hotels: 2026 Limited-Time Hotel Deals @Expedia

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Our top choices for Squirrel Key hotels

A waterfront building with a flat roof, large windows, and a balcony.

A reception area with a wooden sculpture, a reception desk, a computer, and a television.

A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

A beachside dining area with thatched umbrellas, white plastic chairs, and tables.

1. Sugar Loaf Lodge

6.8 km from Squirrel Key

Richard

HK$933

HK$1,050 total

includes taxes & fees

28 Sept - 29 Sept

A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

A residential property with a swimming pool, a covered patio, and a view of the ocean.

A large house with a pool, surrounded by lush greenery.

A concrete pathway flanked by lush green foliage, leading to a shaded area.

2. Atlantic View Luxury Villa with Pool

12.4 km from Squirrel Key

Preetam

HK$4,059

HK$7,655 total

includes taxes & fees

3 Oct - 4 Oct

A marina with boats docked, a pool area, and a building with a white facade.

A clear view of turquoise ocean water and a blue sky with clouds.

A hotel room with a balcony overlooking a marina and the ocean.

A marina with numerous boats docked, a swimming pool, and palm trees.

3. Hilton Key West Resort & Marina

16.5 km from Squirrel Key

Molly

HK$951

HK$1,540 total

includes taxes & fees

29 Sept - 30 Sept

A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.

A marina with boats docked, a swimming pool, and palm trees.

A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

4. The Perry Hotel & Marina Key West

17 km from Squirrel Key

Jade

HK$906

HK$1,499 total

includes taxes & fees

28 Sept - 29 Sept

A balcony with wicker furniture, a view of the sea, and a spiral staircase.

A spacious lobby with a marble floor, leather sofas, and large potted plants.

A modern dining area with a glass table, four chairs, and a ceiling fan.

A beach with palm trees, clear blue water, and a pier extending into the sea.

5. Beachside Resort & Residences

17.6 km from Squirrel Key

James

HK$617

HK$1,444 total

includes taxes & fees

28 Sept - 29 Sept

A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

A wooden dock with a table and chairs, a table lamp, and a toaster.

Three floating cabins with balconies, named Aqua-Lodge, docked on calm water with a clear sky and trees in the background.

A marina with boats docked, a restaurant with outdoor seating, and a building with a blue roof.

6. Aqua Lodges at Hurricane Hole Marina

17.2 km from Squirrel Key

Kagni

HK$770

HK$2,207 total

includes taxes & fees

28 Sept - 29 Sept

A spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.

A multi-story hotel with balconies and a well-lit entrance.

A hotel room with two beds, a balcony with a view of the ocean, and a large wave painting on the wall.

A modern kitchen with white cabinets and a built-in microwave. There is a dining area with a table set for two, a sofa, and a balcony with a view of the ocean.

7. The Laureate Key West

18.1 km from Squirrel Key

Mailyn

HK$1,247

HK$1,624 total

includes taxes & fees

28 Sept - 29 Sept

A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.

A spacious living area with a high ceiling, a blue accent wall, and a wooden staircase.

A hotel with a central courtyard, palm trees, and a fountain.

A spacious indoor dining area with tables and chairs, ceiling fans, and large windows.

8. DoubleTree Resort by Hilton Grand Key - Key West

18.2 km from Squirrel Key

Craige

HK$951

HK$1,335 total

includes taxes & fees

29 Sept - 30 Sept

A pool area with lounge chairs and umbrellas, surrounded by palm trees.

A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.

A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.

A modern office space with a reception desk, computer, and seating area.

9. Fairfield by Marriott Inn & Suites Key West at The Keys Collection

17.7 km from Squirrel Key

Patricia

HK$1,012

HK$1,359 total

includes taxes & fees

28 Sept - 29 Sept

A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.

A couple holding hands in a tropical setting with palm trees and greenery.

10. Blue Flamingo Resort Key West

17.7 km from Squirrel Key

Esteban

HK$927

HK$1,484 total

includes taxes & fees

28 Sept - 29 Sept

A swimming pool with lounge chairs and palm trees.

A modern living room with a sectional sofa, a small round table, and a potted plant.

A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'

11. Hilton Garden Inn Key West / The Keys Collection

17.7 km from Squirrel Key

Walt

HK$823

HK$1,147 total

includes taxes & fees

4 Oct - 5 Oct

A wooden archway leading to a pool area surrounded by lush tropical vegetation.

A beach with palm trees, lounge chairs, and umbrellas.

A beach with palm trees, a sandy shore, and a calm sea under a clear sky.

A tall palm tree with a white building in the background.

12. Parrot Key Hotel & Villas

19.5 km from Squirrel Key

Anthony

HK$996

HK$1,571 total

includes taxes & fees

28 Sept - 29 Sept

A beachside resort with a wooden deck, palm trees, and a sunset view.

A waterfront property with a large building featuring balconies, a pool area, and boats docked in the water.

A dining area with a round table and chairs, a potted plant, and a view of the ocean through large windows with shutters.

13. Grand Marina Suite by Brightwild Waterfront

16.2 km from Squirrel Key

Pawel

HK$2,591

HK$4,820 total

includes taxes & fees

28 Sept - 29 Sept

A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.

A modern restaurant with a wooden counter, seating area, and large windows.

A pool area with lounge chairs, palm trees, and a building with a tiled roof.

A hotel room with a desk, two beds, a TV, a ceiling fan, and a balcony with curtains.

14. Courtyard by Marriott Key West Waterfront

19.1 km from Squirrel Key

Everton

HK$1,404

HK$1,580 total

includes taxes & fees

28 Sept - 29 Sept

A swimming pool surrounded by palm trees and a natural rock formation.

A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.

A covered outdoor seating area with a pool in the background.

A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.

15. Havana Cabana at Key West

18.3 km from Squirrel Key

Silvia

HK$871

HK$1,475 total

includes taxes & fees

28 Sept - 29 Sept

A hotel room with a bed, a view of the beach, a hammock, and beach chairs.

A pool area with blue lounge chairs, a hot tub, and a covered seating area.

A beachfront restaurant with outdoor seating, a seafood sign, and a market sign.

A marina with boats docked, a beach resort building, and palm trees.

16. Ibis Bay Beach Resort

19.1 km from Squirrel Key

Stephanie

HK$795

HK$1,148 total

includes taxes & fees

28 Sept - 29 Sept

17. Island View 1BR Residence With Balcony

17.5 km from Squirrel Key

Luis

HK$1,424

HK$2,331 total

includes taxes & fees

28 Sept - 29 Sept

A lobby with a reception desk, a bar area, and a sign that reads "Tavern Town".

An outdoor bar area with a large island, bar stools, and a pool.

A coastal hotel with multiple buildings, a swimming pool, and a marina with boats.

18. Resort View 1BR Suite

17.5 km from Squirrel Key

Michael

HK$1,424

HK$2,331 total

includes taxes & fees

28 Sept - 29 Sept

A beach view with palm trees, a wooden pier, and a sunset over the water.

19. Ocean Front 1BR Suite With Direct Beach Access

17.5 km from Squirrel Key

Jacqueline

HK$2,019

HK$2,951 total

includes taxes & fees

28 Sept - 29 Sept

A white two-story house with a balcony and a swimming pool.

A balcony with a view of a swimming pool, palm trees, and a fenced yard.

A spacious living area with a wooden dining table, comfortable seating, a flat-screen TV, and a ceiling fan.

A residential building with a covered porch, surrounded by lush greenery and a well-maintained lawn.

20. Capmar House by Brightwild Huge Home Pool

15.6 km from Squirrel Key

Karen

HK$6,132

HK$12,626 total

includes taxes & fees

4 Oct - 5 Oct

View all properties

Compare popular hotels close to Squirrel Key

Property	Property class	Guest rating
Sugar Loaf Lodge	8.2 Very good 1,001 reviews	View
Atlantic View Luxury Villa with Pool	7.4 Good 3 reviews	View
Hilton Key West Resort & Marina	9.0 Wonderful 1,812 reviews	View
The Perry Hotel & Marina Key West	9.4 Exceptional 1,320 reviews	View
Beachside Resort & Residences	8.6 Excellent 2,557 reviews	View

Top Squirrel Key Hotel Reviews

Sugar Loaf Lodge

10/10 Excellent

"Very accommodating! Staff is very friendly! Been coming to Sugarloaf Lodge for many years! Thanks again!"

Sugarloaf Key RV Resort & Cottages

8/10 Good

"Nice for a chill weekend in the lower keys and for people with family accompanying them"

Private Secluded Ocean View & Pool Near Key West

10/10 Excellent

"Great host ! Few snags but it all worked out great."

Oceanside, pet friendly, smart home with plenty of paddle equipment

10/10 Excellent

"nice location, lovely atmosphere in neighborhood"

Private and Exclusive Florida Keys Getaway

10/10 Excellent

"Beautiful view and sweet natural beach/coastline. The pool was heavenly"

Luxurious Oceanfront 5BR Property with heated Pool & Waterfall

10/10 Excellent

"We had an absolutely incredible stay in the Florida Keys this spring! This home exceeded every expectation and was the perfect place for our group of friends and family to relax and enjoy island life. Cris was wonderful to work with — communication was prompt, friendly, and seamless from start to finish.The property was spotless, beautifully maintained, and thoughtfully stocked with everything we needed. The oceanfront setting was stunning, with peaceful mornings by the water and unforgettable sunsets at nearby waterfront restaurants. The outdoor spaces quickly became our favorite place to gather, relax, and soak in the laid-back Keys atmosphere.We loved kayaking from the property, swimming in the clear ocean water, and fishing from the dock. Playing pickleball nearby and walking to the local island coffee shop afterward became one of our favorite routines. The two-story layout with kitchens on both levels was perfect for our group, giving everyone plenty of space and privacy while still feeling connected.The location was ideal — close to restaurants and activities while still peaceful and private. This home created unforgettable memories for all of us, and we would return in a heartbeat. Highly recommend for the perfect Florida Keys getaway!"

Starlight Serenity - Hideaway with Stunning Views

10/10 Excellent

"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"

Waterfront home with a large dock, pool, and deck area. Can accommodate pets.

10/10 Excellent

"This was a lovely home and there was great communication with the host."

Sublimely private luxury home with enveloping oceanfront views near Key West

10/10 Excellent

"We had a wonderful stay at this home. The property itself is absolutely stunning, with beautiful sunset views and a great layout that made it easy for everyone to spread out and relax. The pool was warm and inviting, and there was plenty of space for our group to enjoy both indoors and outdoors. The party room was fun for our teenagers and adults! One of the highlights was the location on the bay—the water is very shallow and incredibly calm, which made it perfect for relaxing and enjoying the surroundings. However, if you’re looking for ocean waves, you won’t get that here. The bedrooms were a pleasant surprise. Although there were no photos listed, they were all very spacious and each had its own en-suite bathroom, which added a lot of comfort and convenience for our group.There were just a couple of things to note. The upstairs bathrooms had low water pressure, which could be improved. Additionally, only four exterior cameras were disclosed in the listing; however, we counted seven cameras around the exterior of the home. Full and accurate disclosure of all cameras is important, and this discrepancy made us feel uncomfortable at times—especially traveling with teenage daughters.Overall, this is a beautiful home in a great setting, and we truly enjoyed our stay."

Other attractions near Squirrel Key

Upper Sugarloaf Sound

9.2/10 (17 reviews)

Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.

See properties

Frequently asked questions

What's the area like around Squirrel Key?

Squirrel Key is located in Summerland Key. You'll find 37 hotels and other accommodations within a few miles for a convenient home base.

What's the best place to stay close to Squirrel Key?

Sugar Loaf Lodge is one of the top choices for your stay based on our traveller data, and this hotel offers a marina and a restaurant. It's located 4.2 mi (6.8 km) from Squirrel Key. Other good choices around the area include Sugarloaf Key RV Resort & Cottages and Sugarloaf Key Hotel at KOA Resort.

How many hotels should I expect to find near Squirrel Key?

Expedia has 37 hotels and other accommodation options a few miles from Squirrel Key.

If I need to cancel the hotel reservation for my stay near Squirrel Key, will I receive a refund?

Yes, most room reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a non-refundable reservation, it might still be possible to cancel it and get a refund within 24 hours of your booking. Plug in your dates, click on "Search", then use the filter option "fully refundable" to review top deals close to Squirrel Key.

Summerland Key Squirrel Key Hotels

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Squirrel Key hotels

1. Sugar Loaf Lodge

2. Atlantic View Luxury Villa with Pool

3. Hilton Key West Resort & Marina

4. The Perry Hotel & Marina Key West

5. Beachside Resort & Residences

6. Aqua Lodges at Hurricane Hole Marina

7. The Laureate Key West

8. DoubleTree Resort by Hilton Grand Key - Key West

9. Fairfield by Marriott Inn & Suites Key West at The Keys Collection

10. Blue Flamingo Resort Key West

11. Hilton Garden Inn Key West / The Keys Collection

12. Parrot Key Hotel & Villas

13. Grand Marina Suite by Brightwild Waterfront

14. Courtyard by Marriott Key West Waterfront

15. Havana Cabana at Key West

16. Ibis Bay Beach Resort

17. Island View 1BR Residence With Balcony

18. Resort View 1BR Suite

19. Ocean Front 1BR Suite With Direct Beach Access

20. Capmar House by Brightwild Huge Home Pool

Compare popular hotels close to Squirrel Key

Top Squirrel Key Hotel Reviews

Sugar Loaf Lodge

Sugarloaf Key RV Resort & Cottages

Private Secluded Ocean View & Pool Near Key West

Oceanside, pet friendly, smart home with plenty of paddle equipment

Private and Exclusive Florida Keys Getaway

Luxurious Oceanfront 5BR Property with heated Pool & Waterfall

Starlight Serenity - Hideaway with Stunning Views

Waterfront home with a large dock, pool, and deck area. Can accommodate pets.

Sublimely private luxury home with enveloping oceanfront views near Key West

Other attractions near Squirrel Key

Upper Sugarloaf Sound

Frequently asked questions